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Retigabine

analytical standard

Synonym(s):

D-23129, Ezogabine, N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C16H18FN3O2
CAS Number:
150812-12-7
Molecular Weight:
303.33
Beilstein/REAXYS Number:
8072099
MDL number:
MFCD04307735
UNSPSC Code:
41116107
PubChem Substance ID:
329769861
NACRES:
NA.24

grade

analytical standard

Quality Level

100

assay

≥98.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

drug control

USDEA Schedule IV

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤1.0% water (calc. from elemental analysis)

application(s)

forensics and toxicology
veterinary

format

neat

storage temp.

2-8°C

SMILES string

FC1=CC=C(CNC2=CC(N)=C(NC(OCC)=O)C=C2)C=C1

InChI

1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)

InChI key

PCOBBVZJEWWZFR-UHFFFAOYSA-N

Gene Information

human ... KCNQ1(3784) , KCNQ2(3785) , KCNQ3(3786) , KCNQ4(9132) , KCNQ5(56479)

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General description

Retigabine is an antiepileptic drug, which activates neuronal KCNQ-type K+ channels by inducing a large hyperpolarizing shift of steady-state activation.

Application

Retigabine may be used as a reference standard in the determination of retigabine in biological matrices using high-performance liquid chromatography coupled with tandem mass spectrometry with positive ion atmospheric pressure chemical ionization (HPLC-APCI-MS/MS).

Biochem/physiol Actions

Retigabine (Ezogabine) is a Kv7.2-7.5 (KCNQ2-5) neuronal potassium channel opener witrh anticonvulsant activity.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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The new anticonvulsant retigabine favors voltage-dependent opening of the Kv7. 2 (KCNQ2) channel by binding to its activation gate.
Wuttke VT, et al.
Molecular Pharmacology, 94, 71-76 (2005)
Determination of retigabine and its acetyl metabolite in biological matrices by on-line solid-phase extraction (column switching) liquid chromatography with tandem mass spectrometry.
Knebel GN, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 748(1), 97-111 (2000)
Identification, characterization, synthesis and HPLC quantification of new process-related impurities and degradation products in retigabine.
Dousa M, et al.
Journal of Pharmaceutical and Biomedical Analysis, 94, 71-76 (2014)
Lyubov I Brueggemann et al.
Molecular pharmacology, 86(3), 330-341 (2014-06-20)
Recent research suggests that smooth muscle cells express Kv7.4 and Kv7.5 voltage-activated potassium channels, which contribute to maintenance of their resting membrane voltage. New pharmacologic activators of Kv7 channels, ML213 (N-mesitybicyclo[2.2.1]heptane-2-carboxamide) and ICA-069673 N-(6-chloropyridin-3-yl)-3,4-difluorobenzamide), have been reported to discriminate among

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